The compounds of the invention are in the field of phenyl-(2-piperidinyl)methanols.
Compounds of the general type are known, e.g., phenylpiperidinylmethanol derivatives in which the phenyl group is substituted in the 4-position by a halogen, lower alkyl, lower alkoxy or methylenedioxy group as described in U.S. Pat. No. 2,928,835. The compound wherein the phenyl ring is 3,4-dimethoxy-substituted is described in British Pat. No. 843,070. The corresponding m-or p-hydroxyphenyl-2-piperidinylmethanols are described in Diss. Abstr. B, 28, No. 7, 2781-2784, Univ. Mich, 1966, the unsubstituted compound .alpha.-phenyl-.alpha.-(2-piperidinyl)methanol is disclosed in British Pat. No. 994,964.
While the compounds described in the above references have physiological activity, they are not known to possess utility as bronchodilator agents.
U.S. Pat. No. 3,705,169 discloses compounds active as bronchodilators wherein an unsubstituted piperidinyl ring is bonded through a hydroxymethyl group to a substituted phenyl ring. However, compounds of the present invention are structurally distinct from the compounds disclosed by this reference in that the present compounds contain an aryl substituted piperidinyl ring. In addition, compounds of the present invention exhibit a significantly longer duration of activity as compared to compounds of this reference, when administered orally to protect against histamine-induced bronchial spasm in animals.